


Charlie the Matchmaker

by thatwriterlady



Series: 30 Day Writing Challenge 2018 [29]
Category: Supernatural
Genre: Attraction, Castiel had a crush on Dean too, Charlie plays matchmaker, Chef Castiel (Supernatural), Chef Dean Winchester, Dean Winchester Has Feelings For Castiel, Dean had a crush on Castiel in high school, Desire, F/F, F/M, Feelings, Flirting, Hurt Dean Winchester, M/M, Misunderstandings, Pining, School Reunion, Sweet, mutual feelings
Language: English
Status: Completed
Published: 2018-11-29
Updated: 2018-11-29
Packaged: 2019-09-02 13:54:38
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,777
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16788247
Author URL: https://archiveofourown.org/users/thatwriterlady/pseuds/thatwriterlady
Summary: When their twenty year high school reunion rolls around, Charlie and her fiancee are happy to find out that all of her old friends had come.  Seeing Dean though, she knew something was wrong.  It doesn't take much to coax out what's on his mind.  His old crush has arrived, and he has a beautiful woman on his arm.  She sees it as a mystery to be solved, and once it is, she decides to play matchmaker.  It isn't high school anymore, and she's going to see Dean face his biggest fear and talk to his crush if it's the last thing she does.





	Charlie the Matchmaker

**Author's Note:**

> Here's Day 29. Sorry it's a little late, I was busy today. I hope you enjoy it.

**Day 29- Calm**

Charlie flicked a piece of lint off her blouse and looked at her fiancée. Gilda was busy tugging her dress down. 

“You ok?”

“Yes, the wind just blew my skirt up and it felt like my rear end was just hanging out,” Gilda smiled sheepishly, making Charlie chuckle.

“Well, it’s not, you’re safe.” Charlie smoothed her hand down the back of Gilda’s dress, reassuring her. 

“Ok, so where exactly are we going?”

“Well, they said the second floor, it’s in a banquet hall,” Charlie took her hand and they headed for the grand staircase in front of them. Gilda was regretting wearing heels, but she’d wanted to look nice for Charlie’s high school reunion. 

When they reached the second floor landing they followed the signs to the right room, and when they stepped through, they took a moment to look around.

“It’s pretty full. Did you expect this many people to come?” Gilda asked.

“No, not really. I expected maybe half this. I wonder how many people brought their significant others,” 

“Charlie? Charlie Bradbury?”

She turned to a table where three women were sitting and smiled.

“Oh my gosh! Donna! How are you?”

Donna smiled cheerily. “I’m great! Come here and sign in, get your name tag!”

Charlie tugged on Gilda’s hand so she followed her, and then signed in. She looked at the other two women who were signing in others. They looked familiar but she couldn’t quite place them. 

“Who’s this with you?” Donna asked.

“This is Gilda, my fiancée. Gilda, this is Donna. She used to hang out with me, Dean, Jo, Ash, and Victor,”

Gilda smiled at Donna and shook her hand when it was offered.

“It’s so nice to meetcha!” Donna smiled back cheerfully. “I’ll get you a blank nametag and you can write your name, and under it, if you want, you can put that you’re with Charlie,”

“Ok,” Gilda accepted the tag and wrote exactly that. She peeled it off the backing and stuck it to her chest.

“Any of the old gang here yet?” Charlie asked. Donna’s smile wavered a bit.

“Yes, all of them, actually. I honestly didn’t expect Ash to come. You know, he still has that mullet? Some things never change,”

Charlie chuckled and looked around. “I am not surprised. Any of them bring someone?”

“Jo is actually married to Ash, if you can believe it. Victor brought his wife.” 

Charlie sighed. “Ok, well, I’m going to go mingle. Will you be able to later?”

“Oh sure, you betcha! We’ll be relieved in about an hour,” Donna replied.

“Come find me, ok?” Charlie nodded towards her.

“I sure will!”

Charlie took Gilda’s hand again and they started walking towards where the tables were.

“She’s…cheerful. Was she always like that?” Gilda asked. Charlie grinned and nodded.

“She was even more cheerful in high school. She’s just a very happy person,”

“I like her, she’s nice,” 

“She’s one of the best people you could ever meet.” Charlie motioned towards an empty table and they headed for it. Gilda sat down, glad to get off her feet. Charlie took a minute to look around. There were so many people she recognized, but there were just as many that she didn’t. Twenty years had done a lot to change them. She spotted a familiar face at the next table and after telling her fiancée she’d be back in a second, she went to say hello.

“Victor Henriksen!”

He turned around, grinning wide when he recognized her.

“Charlie!” He pulled her into a hug, squeezing her tight. “How’ve you been, girl?”

“I’m good, how have you been?”

Victor reached over to a beautiful woman and tugged her closer. “This is my wife, Shana,”

Charlie motioned to Gilda who stood up, tugging her dress down again before walking over to them. “This is my fiancée, Gilda. Gilda, this is Victor and his wife, Shana,”

“It’s nice to meet you, Gilda,” Victor shook her hand while Charlie shook Shana’s.

“So, did you see any of the rest of the gang?” Charlie asked. Victor sighed before nodding.

“Jo’s here, and she’s married to Ash, if you can believe it, but, uh, Dean’s here,”

“Why do I get the feeling you aren’t happy about that?” She asked.

“No, I am, don’t get me wrong, he’s just…,” He shrugged. “I don’t know, but he seems upset.”

“I’ll go find him. I haven’t seen him in about ten years and I miss him. Let me see if I can figure out what’s going on,” She patted Victor’s arm and taking Gilda by the hand, she headed for the crowd gathered near the bar.

“Who is Dean? Is there a reason why he’d be upset?” Gilda asked.

“I can think of a reason,” Charlie was looking around but she hadn’t spotted him yet. “He was in love with a boy back in high school.”

“Ok? I’m not seeing why that would depress him,” Gilda frowned. “What am I missing here?”

Charlie turned to face her. “Well, the boy he was in love with, he had no idea how Dean felt, and Dean never had the guts to tell him because he was way deep in the closet back then. We never knew if his crush even liked guys either. God, Dean pined over him for four long years. He’s out now, and he had a boyfriend the last time I saw him, but we lost touch when he moved from California. He _said_ he was heading to South Dakota, but I have no idea if he actually moved there or not. I was hoping he’d come tonight, or that someone would know how to find him so I could contact him. My guess is that his crush, whose name is Castiel, or Cas as we knew him, is here, and that he’s here with someone. I had no clue he still had feelings for Cas, but if he’s upset, I’m guessing he does. He was my best friend, and I want to see if I can calm him down, get to the bottom of what’s going on,”

“Oh, no, I hope that’s not what’s going on. Let’s find him and make sure he’s ok,” 

Charlie leaned over to kiss her. “You’re amazing,”

“Why, because I want you to help your friend?”

“Because you care about someone you don’t even know. You’re the most perfect angel for me,” She kissed Gilda again, loving the happy smile that lit up her face.

“Let’s find him.”

Charlie squeezed her hand. “Yeah, let’s.”

They ended up stopping to talk to everyone that recognized Charlie, and almost everyone did. Her flaming red hair was quite memorable, and they all wanted to know what she’d been up to, and how she was doing. She introduced Gilda to everyone, most of who were happy for her. A few shut down and cut the conversation short when they realized she was in a same sex relationship. Charlie didn’t have time for those people.

An hour later they’d finally made their way up to the bar, and that was where they found him, staring into a tumbler of whisky.

“Dean?” She slid onto the seat next to him and when he looked up and realized who it was, he smiled wide.

“Charlie! Hey!”

He grabbed her and hugged her tight. She squeezed him back just as tight.

“What are you doing sitting here alone at your high school reunion? This is where you should be socializing, you know, _reuniting_?” She bumped his shoulder and he chuckled.

“Yeah, I did _a lot_ of that already. Jo and Ash are here, Vic too. His wife is a looker. I told her she’s too good for him,” He grinned.

“She seems like a lovely lady. I want you to meet _my_ lovely lady,” She pulled Gilda closer. “This is my fiancée, Gilda. Gilda, this is Dean Winchester, my best friend since the third grade, who thought it was ok to drop off the face of the planet ten years ago,”

Gilda laughed as she shook Dean’s hand. He was laughing too.

“I didn’t mean to do that, Hon, I was going through a rough patch. I got out of a bad relationship, my job fired me, I couldn’t pay my bills, I got evicted, it was just, a really bad time for me. I had to cancel my phone service because I couldn’t pay the bill anymore, and I was crashing on Sam’s couch for like, two months before my uncle told me to come stay with him. That’s about the last time I talked to you. I told you my uncle had told me to come there just before I had to cancel my phone service. At the time I was trying to avoid having to go there, but in the end, I refused to let Sam keep supporting me. I couldn’t get a decent paying job out in Cali. My boyfriend and I had shared the apartment and we split all the bills but when we broke up, he moved out and I couldn’t afford to keep the place. It was a mess, but I moved to South Dakota and my uncle gave me a job at his shop. I went from being a sous chef to being a mechanic, but…my uncle died, and he left me the junkyard and the shop. He also left Sam and me a massive insurance policy. I used my share to open my own restaurant and…now I own three. I still own the shop too, but I have someone else running it,”

“Wow, that is amazing! I’m so happy for you!” Charlie hugged him again.

“What about you, Red? You still doing the computer programming?”

“I am, but I’m doing it for the Pentagon,” She replied.

“Holy, shit,” His eyes blew wide as he stared at her. “Are you serious?”

“I am. That’s where I met Gilda, she’s a programmer too,” Charlie smiled lovingly at her fiancée, and Gilda smiled back.

He looked at his whisky again, turning the tumbler around his hand before picking it up and swallowing down the amber liquid.

“Ok, so why _are_ you sitting here, staring at your drink? Everyone I’ve talked to has told me you’re not looking good. I can tell something’s going on. Talk to me. I’m not leaving until you do,”

He smirked and shook his head. “Typical Charlie,”

She leaned an arm on the bar top and cocked an eyebrow. “Is _he_ here?”

He chewed at the inside of his cheek before nodding. “Yeah,”

“He’s not alone, is he,” 

He shook his head. “No. She’s beautiful, you know? Petite, with long, red hair and big hazel eyes. It’s not like I didn’t expect that he’d find someone gorgeous, I mean, _he’s_ gorgeous, so it really shouldn’t have come as a surprise. I don’t know why I’d expect him to be single after twenty years. Practically no one here is,”

She stood up. “Did you talk to him?”

“No, I didn’t talk to him,” He looked at her like she was nuts.

“Right. You couldn’t talk to him in high school, but I get it, you were a kid, you were scared of rejection, but Dean, you’re almost forty, you can’t keep being afraid. I knew him back then. He was a genuinely nice guy, and not scary at all to talk to. I want to say hi now, see who the woman with him is,”

He didn’t stop her, just stared pathetically after her as she slipped back through the crowd with Gilda. 

It took some searching but she finally found Cas sitting at one of the tables, talking with the other people sitting there too. She recognized most of them, but Cas was the one she wanted to talk to. There was indeed a beautiful red head sitting with him.

“Hi, Cas,”

He looked up, his eyes lighting up with recognition.

“Charlie! Hi!”

He got up and hugged her. “How have you been?”

“I’ve been good, and you?” She asked.

“I’ve been good too. What have you been up to?” He noticed Gilda and smiled as he offered his hand. “I’m Cas.”

“I’m Gilda, Charlie’s fiancée,” 

“Oh, how very nice to meet you,” He was warm and genuine in his greeting, and it made Gilda smile.

“It’s very nice to meet you as well,”

Cas motioned to the woman sitting down watching them and she stood up. Charlie readied herself, waiting to hear who she was.

“Charlie, this is my sister, Anna, Anna, this is Charlie. She was always very nice back in high school,”

Charlie smiled wide. _Not_ his wife. _Not_ his girlfriend. She offered her hand and Anna shook it.

“It’s nice to meet you, Anna,”

“It’s nice to meet you as well. I’ve enjoyed meeting all of my brother’s old friends. He knew some really wonderful people,” Anna offered her hand to Gilda too.

“It has been nice seeing so many familiar faces. Some, not so much. Dick Roman snubbed me, not that I was surprised. He hated me back in high school, so I didn’t expect anything different now. Meg wasn’t exactly friendly either, but I did break up with her kind of coldly sophomore year,” Cas chuckled and shrugged.

“Where are you living? What have you been doing?” Charlie asked.

“I’m a chef, actually. Pastry chef, to be specific. I live in Minnesota. I decided to bring Anna with me because she still lives here,” He looked at his sister and she smiled at him. He smiled back before looking at Charlie again. “What are you doing?”

“I’m a programmer, working at the Pentagon. Gilda’s a programmer too, it’s how we met. We’ve been together for six years now, we’re getting married next year in the spring,” She replied, glancing at Gilda who knew exactly what she was about to do. “So, are you married? Seeing anyone?”

He smiled softly as he shook his head. “No, not in a while,”

“Come with me, I want to introduce you to someone,” She took his hand, not giving him a chance to decline. 

“I’ll stay here, my feet hurt from all the standing,” Anna said sitting back down.

“Right? My feet are _killing_ me!” Gilda lifted her right foot and rotated her ankle. “I’ll sit with Anna, if she doesn’t mind.”

“No, I don’t mind at all,” Anna motioned to her brother’s empty seat and she sat down, sighing with relief. Charlie snickered before dragging Cas across the room.

“Where are we going?” He asked.

“I want to introduce you to another chef,”

“Someone else became a chef?” He was smiling. That was good.

“He’s a chef with multiple restaurants,”

“Who is it?”

She didn’t answer, she just moved past people and headed for the bar. Dean was still sitting there, and she was glad.

“He’s right there,” 

She hadn’t been able to find out if Cas was straight or not, but there really wasn’t a way to gracefully ask that. She marched right up to Dean who, to her surprise was actually drinking a coke instead of more alcohol. 

“Dean,”

He looked up, the start of a smile on his lips, until he realized who was with her. His eyes went wide and she could see how hard he swallowed before forcing the smile back onto his face.

“H-hey,”

“Guess what? Cas here is a chef too,” She looked back at Cas and saw how he was staring at Dean. When he noticed her looking at him he cleared his throat and smiled.

“Hello, Dean, how have you been?” 

“I’ve been good, at least, the last few years or so I have been,” Dean was still nervous, but she counted it as a win that he was at least looking at Cas and talking to him. When Cas sat down on the seat next to him, she stuffed her hands in the pockets of her pants and waited to see what they would say next.

“That’s good to hear. Are you still in Kansas?” Cas asked.

“No, I’m in South Dakota now, what about you?”

“I’m one state over. I’m in Minnesota,” Cas smiled as he motioned to the bartender and ordered a beer.

“You’re a chef?” Dean picked up his coke and took a sip.

“I’m a pastry chef. Where did you go to school?”

“The San Diego Culinary Institute, what about you?” Dean asked.

“I went there too! Small world,” Cas was smiling as he leaned closer. Neither of them noticed Charlie had left. 

“I wonder if we were there at the same time,” Dean was leaning closer too, drawn to the other man. He’d never been able to see Cas’ blue eyes this close up, but he found it impossible not to stare now that they were trained on him. Lord the man was beautiful. “I went to Berkley first to get my BA in business, then I was accepted to culinary school.”

“I went to Stanford, then culinary school. I should have gotten a business degree though,” Cas licked his lips slowly, noticing how Dean followed the motion. He leaned closer and smiled.

“I knew who you were in high school,”

Dean smiled. “Really?”

“Mmmhmm. I knew you were on the baseball team the first two years and the Lacrosse team the last two. I would go to the games with a couple of my friends. I liked watching you play. You were very good; naturally talented at sports. I took classical music and played the violin for quite a few of the school plays, and I was in the tech club. I have pretty good memories of high school,” 

“I knew you were playing for the plays. My brother played flute with you and the other classical musicians. He was a freshman when we were seniors,” Dean said. “You were on the yearbook committee too.”

Cas arched an eyebrow and smiled. “Dean Winchester, were you stalking me?”

Dean blushed and looked down at his drink. “I, um, had a crush on you,” He started when a hand touched his own and he looked up to see Cas had moved closer.

“I liked you too. I saw you freshman year and thought you were cute, but you only got better looking as you got older. The way the girls flocked to you, I wanted to talk to you, but I was really shy back then. That and I thought you were straight,”

“I’m definitely _not_ straight. You really liked me?” Dean couldn’t believe it. He was regretting not talking to him. 

“Yes, really. I think it’s probably good that we didn’t talk to each other back then,” Cas said.

“Why is that?” Dean wondered.

“Because we were kids. We weren’t mature, we had no life experience outside of our town, and we didn’t really know how to control our emotions. We now have that experience, and we’re better able to maintain relationships. It means I can talk to you now without being scared, and I can speak what’s on my mind without getting flustered,”

“What’s on your mind, Cas?”

“I’m thinking that you’re even more handsome than you were in high school. You’re downright gorgeous.”

Dean smiled, feeling more confident than he ever did back then. “How long are you in town for?”

“I’m here for a week, I’m visiting family,”

“Me too. My parents are still here, so I’m staying with them until I go home. I can stay as long as I want since I’m the owner. Would you want to get together while you’re here?”

“I would. I’d like to get to know you, as you are now. I want to learn about you, your interest, your hobbies, and I’d love to know all about your restaurants. I’ll tell you all about me too,” Cas traced circles over Dean’s hand were he still had his own resting.

“We could find a nice, quiet place to do that, just sit and tell one another about our lives,” 

“Do you know what I used to dream about back in high school?” Cas asked. Dean smiled, wondering where he was going with this.

“No, what?”

Cas darted his tongue out to lick the corner of his mouth for a moment, but the way Dean was watching him was really turning him on.

“Kissing you. You were my crush from the first time I saw you. I wasn’t out then though, so all I could do was dream,”

“I was dreaming the same thing,” Dean finished the last of his coke and set the empty glass on the bar top. With his hand free again, he placed it on Cas’ thigh, not caring who saw them.

“Want to get out of here and go make our dreams come true?” Cas was flirting big time, and he loved it. He himself was now eager to leave.

“That sounds like a fantastic idea,”

Cas slid down from his bar stool and took a moment to tug his suit jacket down before smoothing his hand down it.

“I need to let my sister know that I’m going to be indisposed for a while. She’s socializing with Charlie’s fiancée anyway,”

“Indisposed…,” Dean got up and smoothed his own jacket down. “We can be indisposed in my car.”

“Let’s go then,” Cas started walking and Dean happily followed. Victor and his wife were standing by the bar and had heard most of their conversation as they talked to other classmates.

“It’s about time those two told each other how they feel. Watching Dean pine over Cas back then was agonizing for all of us,” Victor said.

“I think they’re both sweet. Who knows? Maybe they’ll fall in love,” Shayna smiled as she watched them disappear in the crowd.

“I think it might be too late for Dean,” Victor joked. Shayna chuckled.

“Well, I’m happy for them. You better make sure you get Dean’s number, and your friend Charlie’s before this is all over. Then you can ask him later when the wedding is,”

Victor let out a surprised laugh. “This is why I love you, your sense of humor matches mine perfectly. I better get an invitation though, or I might just have to crash it,”

“Oh, we’ll get one, no worries there,” She assured him. He kissed her forehead and smiled. Tonight was great so far. All of his old friends were here, and getting to see them again was wonderful. Seeing Dean no longer being melancholy made it all the better. He was actually looking forward to the next reunion, it was looking to be even more interesting than this one.

**Author's Note:**

> Thank you for reading this. One more and we're done. Thank you to those that have followed along and read these all, you're the best!


End file.
